Sodium Hydroxide → HCID 86585364, compound

HRID 635116Notes

Reaction equation

HRID 635116 reaction equation
C([O:3][C:4]([C:6]1([C@H:10]2[CH2:14][N:13]([C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[C:12](=[O:23])[C@H:11]2[F:24])[CH2:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[C:4]([C:6]1([C@H:10]2[CH2:14][N:13]([C@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[C:12](=[O:23])[C@H:11]2[F:24])[CH2:7][CH2:8][CH2:9]1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585362HCID 86585362, compound

Product 1

HCID 86585364HCID 86585364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

cis 4-(1-Ethoxycarbonylcyclobutyl)-3-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone (optical isomer B; 1.79 g, 5.37 mmol) was dissolved in methanol (10 ml) and a 1 N aqueous solution of sodium hydroxide was added dropwise thereinto. The liquid reaction mixture was stirred at 40° C. for 18 hours and then methanol was evaporated under reduced pressure. Water (50 ml) was added to the residue followed by washing with chloroform (100 ml). The aqueous layer thus separated was acidified by dropping 1 N hydrochloric acid thereinto and then extracted with chloroform (100 ml×2). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound in a quantitative amount as a crude product.

Workup

  1. customThe liquid reaction mixture
  2. custommethanol was evaporated under reduced pressure
  3. additionWater (50 ml) was added to the residue
  4. washby washing with chloroform (100 ml)
  5. customThe aqueous layer thus separated
  6. extractionextracted with chloroform (100 ml×2)
  7. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5821d1ac943b4d028a320dfc944f8984
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

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